超分子有机凝胶和水凝胶的制备及其性能研究
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摘要
由小分子量化合物凝胶因子通过分子间氢键、π-π堆砌,以及其它非共价键作用可以形成二维或三维长程有序的超分子聚集体结构进而形成稳定的超分子有机(水)凝胶。由于其性质具有介于固、液体之间这一特性,被广泛应用在催化、纳米材料的模板、药物等分子控制释放载体等广泛领域。
本文合成了几种L-苯丙氨酸衍生物凝胶因子及N-十八烷基马来酸可聚合凝胶因子,研究了其在有机溶剂或水中凝胶化性能及自组装机理。利用水凝胶为水杨酸模型药物的载体,探讨了水杨酸在凝胶中的扩散机理。分别利用L-苯丙氨酸衍生物凝胶因子及N-十八烷基马来酸可聚合凝胶因子在可聚合有机溶剂中的自组装,原位UV固化制备分子印迹聚合物,并考察了相应的印迹聚合物对D-或L-苯丙氨酸的吸附差别。本论文包括以下主要内容:
1、由L-苯丙氨酸和二(三氯甲基)碳酸酯反应得到的L-苯丙氨酸-N-羧基-环内酸酐(L-Phe-NCA),在十八胺的引发下开环聚合得到平均聚合度为5的十八烷基-L-苯丙氨酸齐聚物(简称L-Phe-R18)。L-Phe-R18能在多种有机溶剂中发生聚集、自组装,并进而在这些有机溶剂中形成热可逆的物理凝胶。利用X射线衍射(XRD)和场发射扫描电镜(FE-SEM)表征和分子模拟了L-Phe-R18聚集体的微观形态和可能的聚集方式。
2、合成具有手性结构的L-苯丙氨酸衍生物,3-{[(2R)-2-(十八酰胺基)-3-苯丙基]酰胺基}丁酸四乙基胺盐(简称TC18PheBu)。TC18PheBu在纯水及不同pH值的水溶液中进行自组装,形成超分子水凝胶。利用FE-SEM、POM、FT-IR、荧光探针以及CD观察了TC18PheBu自组装聚集体的形貌并对超分子水凝胶的形成机理进行了探讨。
3、本文利用水杨酸为模型药物分子,研究水杨酸在小分子量凝胶因子TC18PheBu在水中自组装形成的超分子水凝胶中的释药行为。
4、双十八烷基L-苯丙氨酸(Bis18-L-Phe)凝胶因子在可聚合溶剂中以氢键等非共价键相互作用自组装形成直径约为100～200nm的纤维状聚集体,纤维聚集体之间进一步相互作用形成稳定凝胶。以UV光引发原位聚合并将凝胶因子提取制备出非共价键印迹聚合物。为了探讨Bis18-L-Phe分子印迹聚合物对分子识别的机理,重点考察了印迹聚合物对D-和L-苯丙氨酸的pH7.4磷酸盐缓冲水溶液中D-和L-苯丙氨酸的吸附率差别。
5、N-十八烷基马来酸(ODMA)可聚合凝胶因子在可聚合溶剂中以氢键等非共价键相互作用自组装形成稳定凝胶。以UV光引发原位聚合或热聚合并将印迹分子提取制备得到分子印迹聚合物。分别考察了不同聚合方法、不同模板分子以及不同凝胶因子用量对所制得的分子印迹聚合物对D-苯丙氨酸,L-苯丙氨酸磷酸盐缓冲水溶液中的D-和L-苯丙氨酸吸附量的差别。
In recent years, supramolecular hydrogels formed by the self-assembly of gelator through intermolecular hydrogen bonding,π-πstacking and other non-covalent bond interations were applied on catalyzer, nanomaterials, drug carriers and other fields because of its properties between the liquids and solids.
Several gelators based on L-phenylalanine and a polymeric gelator N-Octadecyl Maleamic Acid (ODMA) were synthesized , the properties of gels and the process of self-assembly were investied. Salicylic acid (SA) release from supramolecular hydrogels and the diffusion mechanism of SA was investigated. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the gelator was washed. The adsorbed difference of D- and L-Phenylalanine on MIPs were investied, respectively. This paper are consisted of several sections as the following:
1. The L-phenylalanine-N-carboxyanhydride (L-Phe-NCA) was synthesized from bis(trichloromethyl)carbonate and L-phenylalanine. The average polymerization degree of Octadecyl-L-phenylalanine oligomer is 5 obtained by the ring-open reaction of L-Phe-NCA using octadecylamine as initiator. The morphology and structures of oligomer aggregates in the media were characterized by XRD, FE-SEM and simulated by molecular software.
2. Tetraethylammonium 3-{[(2R)-2-(Octadecylamino)-3-phenylpropanoyl]Amino} butyrate (TC18PheBu), a new hydrogelator based on L-Phenylalaine with chirality was synthesized. It can self-assemble in water or different pH buffer solutions and form into superahydrogels . Suprahydrogels were characterized on using FE-SEM , POM, FT-IR, CD and Fluorescene probe.
3. Release behavior of drug salicylic acid (SA) released from TC18PheBu LMWG hydrogels is invested.
4. The gelator based on N-stearine-N′-steryl-L-Phenylalanine (Bis 18-L-Phe) self-assemble into fibres aggregates through molecular hydrogen bonding and hydrophobic interations in the polymerizable monomer HEMA and crosslinker DPEG200DMA and formed stable gels. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the gelator was washed. The adsorbed difference of D- and L-Phenylalanine on MIPs were investied, respectively.
5. The gelator based on N-Octadecyl Maleamic Acid (ODMA) self-assemble into fibres aggregates between molecular hydrogen bonding and hydrophobic interations in the polymerizable monomer HEMA ,MA and crosslinker DPEG200DMA and formed stable supragels. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the imprinted molecular was washed. The adsorbed efficiency difference of D- and L-Phenylalanine on MIPs prepared by different methods, with different templates molecular and different concentration of ODMA were investied , respectively.
本文合成了几种L-苯丙氨酸衍生物凝胶因子及N-十八烷基马来酸可聚合凝胶因子,研究了其在有机溶剂或水中凝胶化性能及自组装机理。利用水凝胶为水杨酸模型药物的载体,探讨了水杨酸在凝胶中的扩散机理。分别利用L-苯丙氨酸衍生物凝胶因子及N-十八烷基马来酸可聚合凝胶因子在可聚合有机溶剂中的自组装,原位UV固化制备分子印迹聚合物,并考察了相应的印迹聚合物对D-或L-苯丙氨酸的吸附差别。本论文包括以下主要内容:
1、由L-苯丙氨酸和二(三氯甲基)碳酸酯反应得到的L-苯丙氨酸-N-羧基-环内酸酐(L-Phe-NCA),在十八胺的引发下开环聚合得到平均聚合度为5的十八烷基-L-苯丙氨酸齐聚物(简称L-Phe-R18)。L-Phe-R18能在多种有机溶剂中发生聚集、自组装,并进而在这些有机溶剂中形成热可逆的物理凝胶。利用X射线衍射(XRD)和场发射扫描电镜(FE-SEM)表征和分子模拟了L-Phe-R18聚集体的微观形态和可能的聚集方式。
2、合成具有手性结构的L-苯丙氨酸衍生物,3-{[(2R)-2-(十八酰胺基)-3-苯丙基]酰胺基}丁酸四乙基胺盐(简称TC18PheBu)。TC18PheBu在纯水及不同pH值的水溶液中进行自组装,形成超分子水凝胶。利用FE-SEM、POM、FT-IR、荧光探针以及CD观察了TC18PheBu自组装聚集体的形貌并对超分子水凝胶的形成机理进行了探讨。
3、本文利用水杨酸为模型药物分子,研究水杨酸在小分子量凝胶因子TC18PheBu在水中自组装形成的超分子水凝胶中的释药行为。
4、双十八烷基L-苯丙氨酸(Bis18-L-Phe)凝胶因子在可聚合溶剂中以氢键等非共价键相互作用自组装形成直径约为100～200nm的纤维状聚集体,纤维聚集体之间进一步相互作用形成稳定凝胶。以UV光引发原位聚合并将凝胶因子提取制备出非共价键印迹聚合物。为了探讨Bis18-L-Phe分子印迹聚合物对分子识别的机理,重点考察了印迹聚合物对D-和L-苯丙氨酸的pH7.4磷酸盐缓冲水溶液中D-和L-苯丙氨酸的吸附率差别。
5、N-十八烷基马来酸(ODMA)可聚合凝胶因子在可聚合溶剂中以氢键等非共价键相互作用自组装形成稳定凝胶。以UV光引发原位聚合或热聚合并将印迹分子提取制备得到分子印迹聚合物。分别考察了不同聚合方法、不同模板分子以及不同凝胶因子用量对所制得的分子印迹聚合物对D-苯丙氨酸,L-苯丙氨酸磷酸盐缓冲水溶液中的D-和L-苯丙氨酸吸附量的差别。
In recent years, supramolecular hydrogels formed by the self-assembly of gelator through intermolecular hydrogen bonding,π-πstacking and other non-covalent bond interations were applied on catalyzer, nanomaterials, drug carriers and other fields because of its properties between the liquids and solids.
Several gelators based on L-phenylalanine and a polymeric gelator N-Octadecyl Maleamic Acid (ODMA) were synthesized , the properties of gels and the process of self-assembly were investied. Salicylic acid (SA) release from supramolecular hydrogels and the diffusion mechanism of SA was investigated. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the gelator was washed. The adsorbed difference of D- and L-Phenylalanine on MIPs were investied, respectively. This paper are consisted of several sections as the following:
1. The L-phenylalanine-N-carboxyanhydride (L-Phe-NCA) was synthesized from bis(trichloromethyl)carbonate and L-phenylalanine. The average polymerization degree of Octadecyl-L-phenylalanine oligomer is 5 obtained by the ring-open reaction of L-Phe-NCA using octadecylamine as initiator. The morphology and structures of oligomer aggregates in the media were characterized by XRD, FE-SEM and simulated by molecular software.
2. Tetraethylammonium 3-{[(2R)-2-(Octadecylamino)-3-phenylpropanoyl]Amino} butyrate (TC18PheBu), a new hydrogelator based on L-Phenylalaine with chirality was synthesized. It can self-assemble in water or different pH buffer solutions and form into superahydrogels . Suprahydrogels were characterized on using FE-SEM , POM, FT-IR, CD and Fluorescene probe.
3. Release behavior of drug salicylic acid (SA) released from TC18PheBu LMWG hydrogels is invested.
4. The gelator based on N-stearine-N′-steryl-L-Phenylalanine (Bis 18-L-Phe) self-assemble into fibres aggregates through molecular hydrogen bonding and hydrophobic interations in the polymerizable monomer HEMA and crosslinker DPEG200DMA and formed stable gels. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the gelator was washed. The adsorbed difference of D- and L-Phenylalanine on MIPs were investied, respectively.
5. The gelator based on N-Octadecyl Maleamic Acid (ODMA) self-assemble into fibres aggregates between molecular hydrogen bonding and hydrophobic interations in the polymerizable monomer HEMA ,MA and crosslinker DPEG200DMA and formed stable supragels. The molecular imprinted polymers (MIPs) which prepared by in situ UV photopolymerization of self-assembly molecular gels and then the imprinted molecular was washed. The adsorbed efficiency difference of D- and L-Phenylalanine on MIPs prepared by different methods, with different templates molecular and different concentration of ODMA were investied , respectively.
引文
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